The ambitions of cinema and the city have been inextricably connected on many levels since more than a hundred years ago, to the point that many assume that movies were an emblem of urban life in our time. Iranian cities and cinema have not been an exception. Since Lor Girl (1933), the first Iranian sound film, Tehran has played a key role in Iranian cinema either as the backdrop of the story or a character and is represented in images, dialogues, and geographies of the movies. In this lecture, I present a review of urban transformations, characters, and conflicts in Iranian cinema from the 1950s until today. Rural-urban migrations, downtown-uptown conflicts, and the city’s vertical and horizontal expansion are spatial concepts that I interpret to see how the mobile gaze of the cinema establishes our presence in the flow and changes of the city. Through four pre-revolution and four post-revolution images of the city in Iranian cinema, I explore urban characters’ problematics, e.g., heroes and anti-heroes, women, and flâneurs.